CA1067089A - B-aminoethyl silanes and a process for their production - Google Patents
B-aminoethyl silanes and a process for their productionInfo
- Publication number
- CA1067089A CA1067089A CA216,982A CA216982A CA1067089A CA 1067089 A CA1067089 A CA 1067089A CA 216982 A CA216982 A CA 216982A CA 1067089 A CA1067089 A CA 1067089A
- Authority
- CA
- Canada
- Prior art keywords
- beta
- process according
- silane
- ammonia
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 aminoethyl siloxanes Chemical class 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 6
- 229930195734 saturated hydrocarbon Chemical group 0.000 claims abstract description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- 229920006395 saturated elastomer Chemical group 0.000 claims abstract description 4
- 229930195735 unsaturated hydrocarbon Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- VJIFBECQKOBRHM-UHFFFAOYSA-N 2-silylethanamine Chemical class NCC[SiH3] VJIFBECQKOBRHM-UHFFFAOYSA-N 0.000 claims abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 229910021529 ammonia Inorganic materials 0.000 claims description 20
- 229910000077 silane Inorganic materials 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- KCWYOFZQRFCIIE-UHFFFAOYSA-N ethylsilane Chemical compound CC[SiH3] KCWYOFZQRFCIIE-UHFFFAOYSA-N 0.000 claims 5
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 claims 1
- 229920000180 alkyd Polymers 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 229920005989 resin Polymers 0.000 abstract description 4
- 239000011347 resin Substances 0.000 abstract description 4
- 239000000654 additive Substances 0.000 abstract description 2
- 239000003365 glass fiber Substances 0.000 abstract description 2
- 238000005470 impregnation Methods 0.000 abstract description 2
- 238000010348 incorporation Methods 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- QWQNFXDYOCUEER-UHFFFAOYSA-N 2,3-ditert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1C(C)(C)C QWQNFXDYOCUEER-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical class CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Silicon Polymers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2365272A DE2365272A1 (de) | 1973-12-31 | 1973-12-31 | Beta-aminoaethylsilane und verfahren zur herstellung dieser verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1067089A true CA1067089A (en) | 1979-11-27 |
Family
ID=5902290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA216,982A Expired CA1067089A (en) | 1973-12-31 | 1974-12-27 | B-aminoethyl silanes and a process for their production |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4152346A (fi) |
| JP (1) | JPS6038399B2 (fi) |
| BE (1) | BE823973A (fi) |
| CA (1) | CA1067089A (fi) |
| CH (1) | CH606037A5 (fi) |
| DD (1) | DD115685A5 (fi) |
| DE (1) | DE2365272A1 (fi) |
| ES (1) | ES433437A1 (fi) |
| FI (1) | FI374774A (fi) |
| FR (1) | FR2256171B1 (fi) |
| GB (1) | GB1490720A (fi) |
| IT (1) | IT1026195B (fi) |
| NL (1) | NL7417030A (fi) |
| SE (1) | SE418617B (fi) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4394518A (en) * | 1978-02-09 | 1983-07-19 | Wacker-Chemie Gmbh | Organic fibers having improved slip properties |
| CH641470A5 (de) * | 1978-08-30 | 1984-02-29 | Ciba Geigy Ag | Imidgruppen enthaltende silane. |
| US4431832A (en) * | 1979-12-31 | 1984-02-14 | Wacker-Chemie Gmbh | Organic fibers having improved slip properties |
| DE3418358A1 (de) * | 1984-05-17 | 1985-11-21 | Wacker-Chemie GmbH, 8000 München | Verfahren zur herstellung organofunktioneller organopolysiloxane |
| US4584393A (en) * | 1985-01-14 | 1986-04-22 | General Electric Company | Bis(aminoalkyl)disiloxanes and method and intermediates for their preparation |
| US4618689A (en) * | 1985-07-18 | 1986-10-21 | General Electric Company | Novel aminofunctional silicone compositions |
| US4705704A (en) * | 1985-10-01 | 1987-11-10 | General Electric Company | Novel aminofunctional polysiloxane emulsions for treating textiles |
| US4661577A (en) * | 1985-10-01 | 1987-04-28 | General Electric Company | Aminofunctional polysiloxanes |
| JPH07110897B2 (ja) * | 1988-01-29 | 1995-11-29 | 信越化学工業株式会社 | 片末端アミノアルキル停止オルガノシロキサン化合物 |
| US4933413A (en) * | 1989-04-10 | 1990-06-12 | Dow Corning Corporation | Process for synthesis of acylamino organosilicon compounds |
| US5041590A (en) * | 1990-01-04 | 1991-08-20 | Dow Corning Corporation | Quaternary ammonium functional siloxane surfactants |
| US5013577A (en) * | 1990-08-22 | 1991-05-07 | Dow Corning Corporation | Siloxane soluble (CH3)3 SIO1/2 /SIO2 (M/Q) resins with amine and amide organofunctionality |
| US5101056A (en) * | 1990-12-26 | 1992-03-31 | Dow Corning Corporation | Process for converting amino organosilicon compounds to acrylamide organosilicon compounds |
| US5939574A (en) * | 1996-04-15 | 1999-08-17 | Witco Corporation | Aminosiloxanes with 4-amino-3,3-dialkylbutyl groups |
| US5856544A (en) * | 1996-04-15 | 1999-01-05 | Osi Specialties, Inc. | Aminopolysiloxanes with hindered 4-amino-3,3-dimethylbutyl groups |
| WO2011046791A1 (en) | 2009-10-16 | 2011-04-21 | Dow Corning Corporation | Method of producing an aminoalkylalkoxysilane |
| DE102015205341A1 (de) | 2015-03-24 | 2016-09-29 | Wacker Chemie Ag | ß-Aminoalkylgruppen aufweisende Organopolysiloxane und deren Herstellung |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2557803A (en) * | 1950-04-13 | 1951-06-19 | Dow Corning | Bis-amino alkyl siloxanes and their hydrochlorides |
| US2835690A (en) * | 1953-12-31 | 1958-05-20 | Gen Electric | Base-catalyzed addition ot vinyl-silicon compositions |
| US2832754A (en) * | 1955-01-21 | 1958-04-29 | Union Carbide Corp | Alkoxysilylpropylamines |
| US2919173A (en) * | 1958-05-20 | 1959-12-29 | Stevens & Co Inc J P | Dyed fibrous glass material and process of dyeing |
| US2955127A (en) * | 1958-12-29 | 1960-10-04 | Union Carbide Corp | Organosilicon amine oxides and processes for their production |
| US3168389A (en) * | 1960-12-28 | 1965-02-02 | Pittsburgh Plate Glass Co | Silane forming size and glass fiber strands threated therewith for resin reinforcement |
| US3819672A (en) * | 1971-07-12 | 1974-06-25 | Dow Corning | Foaming unsaturated polyester resins |
| US3823098A (en) * | 1971-07-12 | 1974-07-09 | W Joslyn | Foaming unsaturated polyester resins |
| JPS4864031A (fi) * | 1971-12-13 | 1973-09-05 | ||
| US3808018A (en) * | 1972-01-10 | 1974-04-30 | Dow Corning | Primer compositions |
| JPS528854B2 (fi) * | 1972-01-13 | 1977-03-11 |
-
1973
- 1973-12-31 DE DE2365272A patent/DE2365272A1/de active Granted
-
1974
- 1974-11-29 DD DD182678A patent/DD115685A5/xx unknown
- 1974-12-17 US US05/533,728 patent/US4152346A/en not_active Expired - Lifetime
- 1974-12-19 GB GB55045/74A patent/GB1490720A/en not_active Expired
- 1974-12-24 CH CH1731674A patent/CH606037A5/xx not_active IP Right Cessation
- 1974-12-27 FI FI3747/74A patent/FI374774A/fi unknown
- 1974-12-27 JP JP753004A patent/JPS6038399B2/ja not_active Expired
- 1974-12-27 CA CA216,982A patent/CA1067089A/en not_active Expired
- 1974-12-30 IT IT54809/74A patent/IT1026195B/it active
- 1974-12-30 FR FR7443243A patent/FR2256171B1/fr not_active Expired
- 1974-12-30 ES ES433437A patent/ES433437A1/es not_active Expired
- 1974-12-30 SE SE7416358A patent/SE418617B/xx not_active IP Right Cessation
- 1974-12-30 BE BE152029A patent/BE823973A/xx not_active IP Right Cessation
- 1974-12-31 NL NL7417030A patent/NL7417030A/xx active Search and Examination
Also Published As
| Publication number | Publication date |
|---|---|
| FR2256171A1 (fi) | 1975-07-25 |
| DD115685A5 (fi) | 1975-10-12 |
| DE2365272C2 (fi) | 1988-02-18 |
| JPS50100025A (fi) | 1975-08-08 |
| BE823973A (fr) | 1975-04-16 |
| GB1490720A (en) | 1977-11-02 |
| IT1026195B (it) | 1978-09-20 |
| FR2256171B1 (fi) | 1978-09-29 |
| SE7416358L (fi) | 1975-07-01 |
| DE2365272A1 (de) | 1975-07-10 |
| ES433437A1 (es) | 1976-12-16 |
| JPS6038399B2 (ja) | 1985-08-31 |
| US4152346A (en) | 1979-05-01 |
| NL7417030A (nl) | 1975-07-02 |
| SE418617B (sv) | 1981-06-15 |
| FI374774A (fi) | 1975-07-01 |
| CH606037A5 (fi) | 1978-10-13 |
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